The Journal of Organic Chemistry
Article
1-Ethyl-5-hydroxy-4,5-diphenyl-1H-pyrrol-2(5H)-one 2na. The
compound was purified by column chromatography (EtOAc/Pe,
1:2 v/v): 40.2 mg 72% yield; white solid, mp 170−172 °C; 1H NMR
(400 MHz, DMSO) δ 7.69−7.63 (m, 2H), 7.44 (d, J = 7.4 Hz, 2H),
7.34 (t, J = 7.5 Hz, 2H), 7.31−7.23 (m, 4H), 7.10 (s, 1H), 6.78 (s,
1H), 3.17 (dq, J = 14.3, 7.1 Hz, 1H), 2.92 (dq, J = 14.2, 7.1 Hz, 1H),
0.80 (t, J = 7.2 Hz, 3H); 13C{1H} NMR (100 MHz, DMSO) δ 168.6,
159.2, 139.8, 131.0, 129.9, 128.9, 128.8, 128.5, 128.1, 125.9, 120.7,
92.2, 33.2, 14.5; HRMS (ESI) m/z [M + H]+ calcd for C18H18NO2
280.1332, found 280.1332.
5-Hydroxy-1-phenethyl-4,5-diphenyl-1H-pyrrol-2(5H)-one 2ra.
The compound was purified by column chromatography (EtOAc/
Pe, 1:2 v/v): 51.8 mg, 73% yield; white solid, mp 155−157 °C; H
1
NMR (400 MHz, DMSO) δ 7.69 (s, 2H), 7.49 (d, J = 6.9 Hz, 2H),
7.38 (t, J = 7.4 Hz, 2H), 7.30 (s, 4H), 7.26−7.21 (m, 3H), 7.16 (d, J =
7.0 Hz, 1H), 6.99 (d, J = 7.2 Hz, 2H), 6.86 (s, 1H), 3.32−3.24 (m,
1H), 3.09−2.99 (m, 1H), 2.68 (td, J = 12.1, 5.0 Hz, 1H), 2.19 (td, J =
12.2, 5.0 Hz, 1H); 13C{1H} NMR (100 MHz, DMSO) δ 168.8, 159.2,
139.7, 139.6, 131.0, 130.1, 129.1, 128.9, 128.9, 128.7, 128.3, 126.6,
125.9, 120.7, 92.2, 35.1; HRMS (ESI) m/z [M + H]+ calcd for
C24H22NO2 356.1645, found 356.1642.
5-Hydroxy-1-isopropyl-4,5-diphenyl-1H-pyrrol-2(5H)-one 2oa.
The compound was purified by column chromatography (EtOAc/
Pe, 1:2 v/v): 36.9 mg, 63% yield; white solid, mp 187−189 °C; H
NMR (400 MHz, DMSO) δ 7.65−7.59 (m, 2H), 7.47 (d, J = 7.3 Hz,
2H), 7.34 (t, J = 7.5 Hz, 2H), 7.30−7.21 (m, 4H), 7.07 (s, 1H), 6.70
(s, 1H), 3.36 (dd, J = 13.6, 6.8 Hz, 1H), 1.29 (d, J = 6.8 Hz, 3H), 0.90
(d, J = 6.8 Hz, 3H); 13C{1H} NMR (100 MHz, DMSO) δ 168.4,
158.2, 139.6, 131.0, 129.8, 128.7, 128.4, 128.0, 126.0, 121.7, 92.5,
43.4, 21.2, 19.9; HRMS (ESI) m/z [M + H]+ calcd for C19H20NO2
294.1489, found 294.1484.
5-Hydroxy-1,4,5-triphenyl-1H-pyrrol-2(5H)-one 2sa. The com-
pound was purified by column chromatography (EtOAc/Pe, 1:2 v/v):
53.0 mg, 81% yield; white solid, mp 188−190 °C; H NMR (400
MHz, DMSO) δ 7.82 (s, 1H), 7.74 (dd, J = 6.4, 2.8 Hz, 2H), 7.42 (d,
J = 7.7 Hz, 2H), 7.32 (dd, J = 8.8, 5.9 Hz, 4H), 7.26−7.14 (m, 5H),
7.07 (t, J = 7.3 Hz, 2H), 6.95 (s, 1H); 13C{1H} NMR (100 MHz,
DMSO) δ 168.7, 159.8, 139.3, 136.7, 130.9, 130.3, 128.9, 128.8,
128.6, 128.4, 126.1, 125.9, 125.7, 125.7, 120.4, 94.2; HRMS (ESI) m/
z [M + H]+ calcd for C22H18NO2 328.1332, found 328.1329.
1
1
1-Butyl-5-hydroxy-4,5-diphenyl-1H-pyrrol-2(5H)-one 2pa. The
compound was purified by column chromatography (EtOAc/Pe,
1:2 v/v): 43.6 mg, 71% yield; white solid, mp 172−174 °C; 1H NMR
(400 MHz, DMSO) δ 7.66 (s, 2H), 7.43 (d, J = 6.8 Hz, 2H), 7.38−
7.22 (m, 6H), 7.09 (s, 1H), 6.78 (s, 1H), 3.12 (d, J = 9.0 Hz, 1H),
2.83 (dd, J = 13.2, 7.8 Hz, 1H), 1.24 (s, 1H), 1.08 (s, 3H), 0.71 (t, J =
6.7 Hz, 3H); 13C{1H} NMR (100 MHz, DMSO) δ 168.9, 159.1,
139.8, 131.0, 129.9, 128.9, 128.7, 128.4, 128.1, 125.8, 120.7, 92.2,
38.2, 30.9, 20.1, 14.0; HRMS (ESI) m/z [M + H]+ calcd for
C20H22NO2 308.1645, found 308.1641.
4-(2-Chlorophenyl)-5-hydroxy-1-methyl-5-phenyl-1H-pyrrol-
2(5H)-one 2ab. The compound was purified by column chromatog-
raphy (EtOAc/Pe, 1:2 v/v): 41.3 mg, 69% yield; white solid, mp
1
180−182 °C; H NMR (400 MHz, DMSO) δ 7.70 (dt, J = 7.0, 3.4
Hz, 1H), 7.42−7.38 (m, 1H), 7.32−7.23 (m, 7H), 7.20−7.18 (m,
1H), 6.53 (d, J = 2.1 Hz, 1H), 2.58 (s, 3H); 13C{1H} NMR (100
MHz, DMSO) δ 168.6, 156.7, 137.8, 133.0, 130.7, 130.7, 130.5,
130.2, 128.9, 128.7, 127.1, 126.2, 125.9, 93.5, 24.0; HRMS (ESI) m/z
[M + H]+ calcd for C17H15ClNO2 300.0786, found 300.0782.
1-Benzyl-5-hydroxy-4,5-diphenyl-1H-pyrrol-2(5H)-one 2qa. The
compound was purified by column chromatography (EtOAc/Pe, 1:2
1
4-(3-Fluorophenyl)-5-hydroxy-1-methyl-5-phenyl-1H-pyrrol-
2(5H)-one 2ac. The compound was purified by column chromatog-
raphy (EtOAc/Pe, 1:2 v/v): 44.7 mg, 79% yield; white solid, mp
163−165 °C; 1H NMR (400 MHz, DMSO) δ 7.50 (dd, J = 15.3, 4.8
Hz, 2H), 7.43−7.33 (m, 5H), 7.32−7.27 (m, 1H), 7.21 (s, 1H), 7.15
(td, J = 8.6, 2.3 Hz, 1H), 6.92 (s, 1H), 2.47 (s, 3H); 13C{1H} NMR
v/v): 60.0 mg, 88% yield; white solid, mp 215−217 °C; H NMR
(400 MHz, DMSO) δ 7.68 (s, 2H), 7.40 (s, 2H), 7.32−7.16 (m, 7H),
7.16−6.98 (m, 5H), 6.91−6.83 (m, 1H), 4.28 (d, J = 15.6 Hz, 1H),
4.08 (d, J = 14.8 Hz, 1H); 13C{1H} NMR (100 MHz, DMSO) δ
169.3, 159.6, 139.4, 138.8, 131.1, 130.0, 128.8, 128.8, 128.4, 128.2,
128.1, 128.1, 126.7, 126.0, 120.5, 92.4, 42.3; HRMS (ESI) m/z [M +
H]+ calcd for C23H20NO2 342.1489, found 342.1492.
1
(100 MHz, DMSO) δ 168.3, 162.3 (C−F, JC−F = 242.9 Hz), 158.2,
3
3
138.8, 133.4 (C−F, JC−F = 8.3 Hz), 130.9 (C−F, JC−F = 8.4 Hz),
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J. Org. Chem. 2021, 86, 2917−2928